Find Hotels with a Pool in Stockbridge, MA

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Stockbridge Hotels with a Pool

Next weekend
May 29 - May 31
In two weeks
Jun 5 - Jun 7

Our top choices for Stockbridge hotels with a pool

Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
"The pool and hot tube were open, maybe bring a swimsuit if you are up for a soak in the hot tub on a cold snowy day or night."
United States
Judith Pauline
$184 nightly
The price is $206
May 31 - Jun 1
Total with taxes and fees
The Red Lion Inn
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (111 reviews)
  • cleanliness
    Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
"The Stockbridge Country Inn is the quintessential New England B&B! The owner, Diane, is the perfect host - very friendly and knowledgeable about the area. We stayed in The Maid's Suite which was extremely comfortable and beautifully decorated. Breakfast was always a delicious treat! The convenient location made access to sightseeing so easy."
United States
Linda
$358 nightly
The price is $399
Jun 7 - Jun 8
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
"the hot tub and pool I spent some time relaxing in after check-in"
United States
Nicholas
$109 nightly
The price is $122
May 26 - May 27
Total with taxes and fees
The Yankee Inn
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (946 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
"Spacious, clean, and the pool was warm and perfect for family swimming"
United States
Danielle
$113 nightly
The price is $126
May 25 - May 26
Total with taxes and fees
Berkshire Mountain Lodge
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
"Nice pool and gym facility."
United States
Melanie
$122 nightly
The price is $136
May 28 - May 29
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Outdoor spa tub

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,363 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
"Spacious suite, comfortable bed and the view of the ski slopes from the large indoor pool was amazing."
United States
Ellen
$108 nightly
The price is $120
May 31 - Jun 1
Total with taxes and fees
Vacation Village in the Berkshires
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
"we loved using the pool at the beautiful Red Lion"
United States
Lisa
$95 nightly
The price is $106
Jun 11 - Jun 12
Total with taxes and fees
The Little Lion
Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (182 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
"Pool was perfect."
United States
Diane
$143 nightly
The price is $164
May 25 - May 26
Total with taxes and fees
Blackberry River Inn
Indoor pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (766 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
"This is not my first stay. Great hotel to stay for ski trips "
United States
Michael
$124 nightly
The price is $139
Jun 1 - Jun 2
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Seasonal outdoor pool

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (97 reviews)
  • cleanliness
    Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
"The pool is well maintained and cleaned."
United States
Geraldine
$104 nightly
The price is $114
May 26 - May 27
Total with taxes and fees
The Springs Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Stockbridge

Breakfast included
Hot tub

Top Stockbridge Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"Excellent value, I had a great experience. The breakfast was a cut above, but they didn't include any fresh fruit. Maybe that's nit-picking. I'd recommend it, especially to families. Lots of good restaurants nearby."
judith 1-night trip
Posted 6 hours ago
The Yankee Inn

Frequently asked questions

What are the best hotels in Stockbridge with outdoor pools?
The Red Lion Inn is a charming 3.5-star hotel that offers an inviting outdoor pool, great for families looking to unwind after a day of adventure in the beautiful Berkshires. Guests rave about the comfortable and quiet rooms, as well as the excellent food and friendly service provided by the staff. Plus, its prime location in a historic district means you're just a stone's throw away from local attractions, including nearby ski areas for winter sports enthusiasts.

For a more intimate experience, consider The Stockbridge Country Inn, rated 4.5 stars by travellers. This delightful bed and breakfast not only features an outdoor pool but also provides complimentary full and continental breakfasts, ensuring a great start to your day. With its proximity to the Norman Rockwell Museum and picturesque mountain views, it's an ideal spot for families seeking both relaxation and cultural enrichment. Guests particularly appreciate the peaceful atmosphere and the opportunity for mountain biking right on-site.
How much does a hotel with outdoor pool in Stockbridge cost?
Enjoy staying in a hotel in Stockbridge with an outdoor pool. You can find a great deal from $106 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Is it cheaper to book flights and a Stockbridge hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
How can I save on a Stockbridge hotel with a pool with Expedia?
Before booking your Stockbridge hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Stockbridge for you.

Explore a world of travel with Expedia